84569-94-8Relevant academic research and scientific papers
A highly diastereoselective chiral pool based synthesis of cis- and trans- indan-1,2-diols
Sengupta, Saumitra,Mondal, Somnath
, p. 3469 - 3470 (1999)
Starting from the α-hydroxy acid chiral-pool, the 1R,2S- and 1S,2S- indan-1,2-diols have been prepared in a few steps with excellent diastereoselectivity.
Synthesis of 4,4′-biquinazoline alcohols as chiral catalysts in enantioselective alkynylation of aldehydes with phenyl acetylene
Catir, Mustafa,Cakici, Murat,Karabuga, Semistan,Ulukanli, Sabri,Sahin, Ertan,Kilic, Hamdullah
experimental part, p. 2845 - 2853 (2010/04/02)
Optically active propargylic alcohols are important chiral-building blocks in asymmetric synthesis, while the asymmetric addition of a terminal alkyne to an aldehyde is one of the most important procedures to prepare these chiral-building blocks. In this work, a family of chiral 4,4′-biquinazoline alcohols has been conveniently prepared from the easily accessible (S)-2-acetoxycarboxylic acid chlorides by reaction sequences beginning with condensation and followed by key synthetic steps including chlorination, nickel(0)-mediated homocoupling, and deprotection in addition to being examined as potential ligands in the enantioselective addition of phenylacetylene to aldehydes. These chiral ligands can be combined with Ti(OiPr)4 and then used to catalyze the asymmetric addition of zinc acetylide, produced in situ by the reaction of phenylacetylene with diethylzinc, to aldehydes. The best enantiomeric excess obtained in this study was 75%.
Trichosporon cutaneum-promoted deracemization of (±)-2-hydroxindan-1-one: a mechanistic study
Cazetta, Tarcila,Lunardi, Ines,Conceicao, Gelson J.A.,Moran, Paulo J.S.,Rodrigues, J. Augusto R.
, p. 2030 - 2036 (2008/02/11)
A mechanistic study of the deracemization of (±)-2-hydroxy-1-indanone mediated by the yeast Trichosporon cutaneum to afford pure (1S,2R)-1,2-indandiol is reported. The key aspect of the study was the use of pure (R)- and (S)-2-hydroxy-1-indanone enantiomers to ensure reliable conclusions. Experiments in the absence of yeast cells or using dead cells disclosed that the pure enantiomers were not racemized, which suggest that the whole dynamic kinetic resolution process is enzymatic in character. When living yeast cells were used the (R)-substrate was smoothly converted to (1S,2R)-1,2-indandiol, whilst the (S)-2-hydroxy-1-indanone was converted to the same diol through a more complex fashion, which requires a more lengthy oxidation-reduction pathway having the 1,2-indanedione as an achiral intermediate. An unexpected observation was that 1,2-indanone acts as a moderate inhibitor of the reductive enzymes acting in the conversion of (R)-2-hydroxy-1-indanone to (1S,2R)-1,2-indandiol.
Cyclic AMP-specific phosphodiesterase inhibitors
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, (2008/06/13)
Novel pyrrolidine compounds that are potent and selective inhibitors of PDE4, as well as methods of making the same, are disclosed. Use of the compounds in the treatment of inflammatory diseases and other diseases involving elevated levels of cytokines, as well as central nervous system (CNS) disorders, also is disclosed.
A simple procedure for the synthesis of enantiopure α-acetoxy ketones
Babudri, Francesco,Fiandanese, Vito,Marchese, Giuseppe,Punzi, Angela
, p. 2431 - 2440 (2007/10/03)
Cross-coupling reactions of α-acetoxy carboxylic acid chlorides with organocopper reagents, derived from Grignard reagents, cuprous bromide and lithium bromide, provide a simple and straightforward method for the synthesis of enantiopure α-acetoxy ketones.
A facile synthesis of enantiopure γ-amino- and γ-hydroxy-β- ketosulfones
Sengupta, Saumitra,Sen Sarma, Debarati,Mondal, Somnath
, p. 4409 - 4417 (2007/10/03)
Enantiopure γ-amino and γ-hydroxy-β-ketosulfones have been synthesized in high yields from α-diazoketones derived from the α-amino and αhydroxy acid chiral pools.
γ-amino-β-ketosulfones as chiral educts: A facile synthesis of enantiopure α-amino ketones
Sengupta, Saumitra,Sen Sarma, Debarati,Mondal, Somnath
, p. 9791 - 9798 (2007/10/03)
Starting from 'chiral-pool' derived γ-amino-β-ketosulfones, a facile synthesis of enantio-pure α-amino ketones has been developed via an α- alkylation-desulfonation sequence. Extension of this methodology to enantiopure α-acetoxy ketone synthesis, however, have met with limited success.
Enantioselective Preparation of α-Acyloxy Ketones from α-Hydroxy and α-Amino Acids
Cahiez, Gerard,Metais, Eric
, p. 6449 - 6452 (2007/10/02)
Various chiral α-acyloxy ketones have been easily prepared, in high yields with an excellent enantiomeric purity, by acylation of organomanganese reagents with the corresponding α-acyloxy carboxylic acid chlorides prepared from α-hydroxy and α-amino acids.
